Shawn Ryan Show #229: AJ Gentile – Creator & Host of The Why Files

Release Date: August 21, 2025
Host: Shawn Ryan
Guest: AJ Gentile

Episode Overview

This episode features AJ Gentile, the creator and host of the massively popular YouTube channel The Why Files, known for exploring mysteries, myths, conspiracies, and the unexplained. AJ joins Shawn Ryan for a wide-ranging, deeply candid conversation on the ups and downs of content creation, personal vulnerability, government secrecy, and why critical thinking is vital in today’s world. The episode dives into AJ's origins, the explosion of The Why Files, government mistrust, ancient mysteries, and much more.

Key Discussion Points & Insights

1. Opening & Introductions

[00:39-02:41]

• Shawn shares his admiration for AJ’s work: “You are what me and my wife watch just about every night... to meet you is pretty surreal.”
• AJ reciprocates: “It’s exciting for me... I’m a fan.”
• Shawn gifts AJ a Sig Sauer pistol, leading to a light, friendly exchange about shooting and firearms.

2. The Emotional Weight of Content

[04:36-11:22]

• Patreon Question: “Have you ever found info in your research that was bigger than you wanted to touch?”
• AJ recounts his episode on DARPA and Agent Orange, and how it struck a personal nerve:
  • “...my father-in-law suffers from everything... every illness you can have from Agent Orange.”
  • He wrestled with releasing such a heavy episode, but was motivated by the outpouring of thanks from veterans.
• Discussion ensues about bureaucracy and the challenges veterans face accessing their benefits.
• Shawn relates with his own difficult post-military experiences and shares resources to support veterans, emphasizing the systemic neglect:
  • “...when your country needs you, you answer the call; but when you need your country, take a number.” – AJ ([06:06])

3. AJ’s Path to The Why Files

[11:42-22:11]

• Raised in the Bronx, dabbled in stand-up, radio, and production.
• Multiple failed businesses and podcast studios; LA civil unrest led to relocating to AZ.
• COVID lockdowns pushed him to launch The Why Files on YouTube:
  • “If I knew how hard it was, I probably wouldn’t have had the stamina to stick with it.” – AJ ([18:58])
• Faced struggles with early YouTube algorithm, authenticity, and audience-building before eventual viral growth.

4. Authenticity & Vulnerability in Content Creation

[22:12-27:45]

• Both discuss the challenges and necessity of being genuine and vulnerable on camera:
  • “Just be yourself. Be authentic, let all the wounds show.” – AJ ([22:12])
  • “People are scared to death of authenticity...” – Shawn ([22:40])
• AJ’s direct, honest engagement with fans has been powerful for both him and his audience.

5. The Professional “Hockey Stick” Moment

[29:17-32:53]

• Stagnant for 2 years, the channel’s growth exploded when TikTok Shorts went viral.
• “My video started hitting a million in a month... now we hit a million views in 16 hours.” – AJ ([32:53])

6. On Anxiety, Loss Aversion, and Therapy

[36:07-42:52]

• AJ shares his lifelong struggles with anxiety and fear of losing success.
• He built an AI therapist using his own data:
  • “Apparently I suffer from loss aversion—when I have something, I’m worried it’ll be taken away.” – AJ ([37:34])
• Shawn offers his perspective on preparing psychologically for endings, and the importance of valuing what exists beyond material success:
  • "If it does all end, I go back to that…It’s just a new chapter." – Shawn ([42:09])

7. Building Legacy & The Value of Vocation

[44:14-47:20]

• Both reflect on how podcasts/YouTube aren’t easily transferable as businesses or legacies, prompting new ventures and companies.
• Discuss the difference between a career and a vocation—pursuing what they’re meant to do:
  • “Vocation is a calling, not a job... I’m meant to do this, connecting and entertaining people.” – AJ ([46:19])

8. The Importance of Critical Thinking

[47:20-49:19]

• Shawn praises The Why Files’ ability to give the audience space to think for themselves:
  • “You present all the conspiracies and facts, and you force people to think.” – Shawn ([47:20])
• AJ: “I’m not here to convince anyone. I’m not a pundit or conspiracy theorist. I just enjoy the stories.” ([48:25])

9. Format & Approaching Guests/Stories

[49:39-57:40]

• Shawn and AJ discuss their selective processes for topics and guests, rejecting “big names” unless genuinely interested.
• Value of audience feedback and the organic evolution of their channels.

Deep Dives into Mystery & Conspiracies

1. Moon Landing Theories

[66:49-74:38]

• AJ’s moon landing episodes:
  • Presents various anomalies (lost tapes, reflection/shadow issues, radiation) but debunks some popular theories.
  • “They lost the technology to go back… the Van Allen Radiation Belt is a big unexplained.” – AJ ([70:23])
• Discussion connects modern government distrust with increased skepticism about the moon landing.
• “Every Covid conspiracy I talked about just came true.” – AJ ([73:15])
• Reflection on how lack of transparency across events (Epstein, Russiagate, etc.) erodes public trust.

2. Government Corruption, Patriot Act, & Surveillance

[126:14-147:22]

• Origins of the Patriot Act, government abuse, and implications of mass surveillance.
  • “They were capturing everything, not just metadata.” – AJ ([126:43])
  • Use has shifted—now mostly targets drugs/domestic issues, not terrorism; bipartisan support continues.
• Discussion of the abuse of surveillance against political enemies and parents at school board meetings.
• AJ: “I’m political, but not ideological...anti-government, pro-transparency, anti-corruption.” ([80:45])
• Both agree: Independent voices and platforms now have more reach and power than legacy media.

3. Ancient Mysteries: Pyramids, Easter Island, Giants, and More

[88:24-120:10]

• The Moon seeming “hollow” based on seismic experiments; unexplained lights and geological oddities.
• Pyramids as possible ancient power plants:
  • “Guns in my head, I think they [pyramids] were used to generate energy... the Egyptians didn't build any of this.” – AJ ([101:35])
• The Sphinx’s water erosion, Easter Island’s buried moai, and Stonehenge’s advanced engineering.
• Giants in ancient lore—biblical Nephilim, the Smithsonian “cover-ups,” disproving and examining evidence ([182:24]-[201:08]).
• The Book of Enoch and alternative biblical texts:
  • “The Book of Enoch expands on all of that… what it sounds like he’s describing is a spacecraft.” – AJ ([198:00])

4. The Vatican & Strange Artifacts

[204:35-210:01]

• Rumors around the Vatican’s secret archives: Spear of Destiny, Ark of the Covenant, and the “Chronovisor” (alleged time-viewing device).
• Many artifacts and documents remain hidden from public view.

5. Classic Weirdness: Mel's Hole, Bigfoot, and Cryptids

[213:40-228:22]

• Retelling of Mel's Hole—endless pit in Washington state with supernatural properties. AJ unpacks the Art Bell classic and how even debunked stories inspire wonder.
• Brief on Bigfoot, Loch Ness, and other cryptids: “The evidence always sucks, but people love those stories.”
• AJ’s signature approach: present the legend, then seek the facts.

Notable Quotes & Memorable Moments

• On Government and Disinformation:

  • “If you’re on the left and think the right is the problem, or on the right and think the left’s the problem—you’re the problem.” – AJ, ([85:01])
  • “The media is over. It will die with the baby boomer generation.” – Shawn ([150:09])

• On Creative Vocation:

  • “If you love it and you’re good at it… vocation is a calling.” – AJ ([46:19])

• On Transparency and Legacy:

  • “I don’t want power. I just want to entertain people and get them thinking differently.” – AJ ([58:12])

• On Vulnerability:

  • “I’m the most honest in my life when I’m talking on that [livestream] to the people who watch the show…” – AJ ([27:39])

Timestamps for Key Segments

• [04:36] – AJ on the “Dark Side of DARPA” & the emotional cost of content
• [11:42] – Early life, failed businesses, moving to AZ
• [22:12] – Authenticity, letting the guard down as a creator
• [29:17] – When The Why Files “hockey sticked” into virality
• [36:07] – On anxiety, fear of loss, and using AI for therapy
• [47:20] – Critical thinking in the age of conspiracies
• [66:49] – Moon landing debates (tapes, technology, skepticism)
• [88:24] – Is the Moon a hollow structure?
• [101:35] – Pyramids as ancient power plants and lost civilizations
• [126:14] – Patriot Act, mass surveillance, and national security states
• [182:24] – History and legends of giants, Smithsonian’s alleged role
• [204:35] – Vatican secret archives and the Chronovisor
• [213:40] – Mel’s Hole and legendary American weirdness
• [226:04] – Bigfoot and the skeptical side of cryptid lore

Closing Thoughts

Throughout the conversation, AJ and Shawn emphasize the need for skepticism, humility, and introspection—whether dealing with conspiracy theories, government overreach, or personal demons. The Why Files succeeds because it respects the mystery while never losing sight of the facts—“I just pull the threads and I lay it out… I’m fascinated, not saying I believe any of it.”

They close by teasing AJ’s new studio and plans for future conversations, pledging mutual support as members of a rare, growing class of independent creators exploring our weird and wonderful world.

“Just be yourself. Be authentic. Be raw. Let all the wounds show.” – AJ Gentile ([22:12])